Have you ever felt like something in your life no longer fits, even though you can’t quite explain why?

You may feel lost, disconnected, or unsure of who you are anymore. From the outside, life may look good. And yet something inside feels unsettled. As though you’re being pulled toward something you don’t fully understand.

This experience can feel confusing, even unsettling. But what if it’s not a problem to fix? What if it’s the beginning of something much more important, and what many wisdom traditions call awakening?

I remember standing on top of Mount Kilimanjaro, where I thought I would feel on top of the world. Instead, I felt lower than I ever had. Despite having everything I thought I wanted, I felt empty, lost, confused, and stuck. I didn’t know it then, but I was at the beginning of the awakening process and the beginning of understanding myself in a way I never had before.

What Awakening Actually Is

Awakening, as I’ve come to understand it, is not about transcending our human experience. It’s about fully embodying it by becoming aware of our dual nature.

We each carry two distinct energies within us. I call them the conditioned self and the soul.

The Conditioned Self

The conditioned self, what the wisdom of the Enneagram calls the personality, is the part of us that developed in response to the world. It learned what was needed to feel safe, to belong, to be loved and accepted. It built strategies, patterns, and beliefs: be good, be useful, be enough, don’t make waves, don’t ask for too much.

The conditioned self isn’t the enemy. It’s not bad. It helped us survive and adapt. But it was never designed to help us thrive. When the conditioned self is driving the bus, when our choices, our relationships, our sense of worth are all filtered through its fear-based lens, we feel the quiet cost of it. We feel disconnected. We feel like something is missing. We feel, despite everything, not quite ourselves.

The Soul

The soul is the truth of who we are. It’s the part that thrives on freedom, expansion, growth, and genuine self-expression. Its deepest desire isn’t to achieve more, but to become more. It’s shy, and it reveals itself only in quiet moments, when we’re still enough to listen.

The soul doesn’t communicate in demands or crises. It speaks in gentle nudges, a restlessness that won’t settle, a longing that doesn’t go away, a quiet sense that the life you’re living doesn’t fully match the life you’re meant to be living. I wrote an article where I shared what I had learned from over a decade of asking the question, What is the Soul? It’s a powerful question that helps us discern whether what we’re experiencing is arising from our personality or our soul energy.

The Moment They Become Distinct

Awakening is the moment we begin to feel these two energies as distinct and start to sense the difference between what the conditioned self has built and what the soul is asking for. When the personality’s strategies start to feel hollow. When the soul’s longing becomes too persistent to ignore, and what I’ve come to call soul hunger begins to rise in us, we’re beginning to awaken.

This is why awakening so often feels like being pulled in two directions at once. Not because something is wrong. Because something is waking up in us.

How Awakening Actual Feels: Five Signs

Awakening rarely arrives with clarity or fanfare. More often, it arrives as a series of subtle but persistent shifts and the felt experience of the dual nature becoming conscious.

If you’re wondering whether something deeper is unfolding in you, you may recognize yourself in what many people have shared with me over the years:

1. A Sense That Something Is Missing — Even When Life Looks Good

You may look at your life and know, objectively, that it’s good. And yet something feels off. A quiet emptiness, a lack of lustre, a feeling that something essential hasn’t been found. This is often the first signal from the soul that the small self’s world no longer satisfies what the deeper part of you is hungry for.

2. You Don’t Know Who You Are Anymore

Questions begin to surface: Who am I beyond my roles? What do I actually want? Why does it feel like I’ve lost myself? You may feel like there are two versions of you — the one who shows up in the world, and another part that feels harder to access. This is the gap between the conditioned self and the soul becoming conscious. It’s disorienting, but also the beginning of something more honest.

3. You Feel Lost, Directionless, or Without Purpose

Even if you have goals or things you ‘should’ be doing, it can feel difficult to connect with the energy or motivation to follow through. This isn’t a failure of discipline or drive. It’s often what happens when your life is no longer being guided by something that feels true to you at the soul level.

4. You Begin to See the Ways You’ve Been Living Behind a Mask

As awareness deepens, you start to notice how often you adapt, perform, or override your own needs. You begin to see the roles you’ve taken on, the expectations you’ve tried to meet, the ways you’ve shaped yourself to belong. There can be a quiet realization: I’ve been living from my conditioned self, I’ve been living from the outside in. That awareness is not a failure; it’s the beginning of something more authentic.

5. Your Body and Inner World Feel Unsettled

Sometimes, awakening is felt most clearly in the body. More tired than usual. Emotionally reactive. Unable to fully settle, even when life on the surface seems manageable. Sleep disrupted. Energy fluctuating. This is often the nervous system responding to an inner disconnection that is asking to be seen. It’s the soul’s way of making itself heard when quieter signals have been ignored.

Where Awakening Leads: The Dark Night and the Path Through

Books have been written about awakening — whole libraries of them. I don’t want to reduce it to a list of signs. What I can offer is what I’ve come to understand through my own journey and through walking alongside others in theirs.

Awakening often moves through what is called the dark night of the soul — though I’ve come to think of it more precisely as the dark night of the personality. It’s the period when our conditioned self-strategies and the identity we’ve built around them begin to loosen and unravel. The foundation feels less stable. Things that once brought comfort or meaning may feel empty. The old no longer fits, and the new hasn’t yet arrived.

This isn’t a sign that something is broken. It’s a passage — the personality shedding what no longer serves so the soul can take its rightful place. As James Hollis wrote:

There is no going forward without a death of some kind: a death of who we thought we were and were supposed to be… But life has other plans; indeed, our own souls have other plans.

Not everyone experiences awakening as a dark night. For some, it’s quieter, a gradual loosening, a growing restlessness, a slow shift in what matters. But for many, there is a period of genuine disorientation before the new self begins to emerge.

If you sense you may be in that territory, I explore it more fully in What Is The Dark Night of the Soul? It’s Not What You Think.

What Awakening Is Really Asking Of You

Awakening isn’t asking you to leave your life behind, transcend your humanity, or become someone entirely different.

It’s asking you to come into a more loving, conscious relationship with yourself — with the fullness of who you are. Both the conditioned that learned to adapt and the soul that is ready to grow. Not eliminating one in favour of the other, but learning to live from a place where the soul guides and the conditioned self serves.

Most of us were never taught how to do this. We were taught how to achieve, adapt, perform, and keep going. But very few of us were given the tools to understand our own inner world — to know our patterns, settle our nervous system, and hear the quieter voice of our soul beneath the noise of daily life.

That’s what the awakening journey is ultimately building: a relationship with yourself that is honest, loving, and grounded enough to live from the inside out.

When that relationship begins to strengthen, something shifts. Not all at once. But gradually, the confusion gives way to clarity. The restlessness settles into purpose. The sense that something is missing transforms into a sense of coming home.

Because the truth is, awakening isn’t the beginning of losing your way. It’s the beginning of finding your way back to yourself.

If you’re in the middle of this and it feels more disorienting than enlightening — that’s normal. Awakening rarely arrives with clarity. It arrives with questions. And the most important thing in the early stages is not to rush toward answers, but to begin building the inner conditions where your own wisdom can be heard.

For me, that began with a simple meditation practice. Not because it fixed anything, but because it created the first genuine quiet I’d had in years — and in that quiet, I began to find my way back. If you’re looking for a place to begin, A Simple Daily Meditation Practice for Calm, Clarity and Resilience is a good place to start.

If you sense that what’s unfolding in you needs more than a practice — that you’re ready for a guide who has walked this path and can help you understand your patterns, settle your nervous system, and build a more loving relationship with yourself — I’d love to support you. My three-month Mindfulness Coaching programme is designed for exactly this journey. You’re welcome to reach out.

And if this post reminds you of something you’ve been living — I’d love to hear about it. Leave a comment below.